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BlueStone Tech
Server 2016 EOL: 12 January 2027

Windows Server 2016 stops getting security updates on 12 January 2027.

Here's the Melbourne SMB migration path — three fixed-price packages, dates in writing, no procurement theatre.

Time until Microsoft pulls the patches
—days
·
—hours
·
—mins
Get a free migration quote See fixed-price packages

Same-business-day email reply. No phone calls unless you ask for one.

After 12 January 2027

Three things change overnight.

Security

CVEs stop being patched.

On 13 January 2027, every new Server 2016 vulnerability becomes permanently exposed. Ransomware crews already scan for unpatched servers — that exposure compounds every week.

Compliance & insurance

Cyber insurance gets harder.

Renewal questionnaires now ask explicitly about EOL operating systems. Policies are being written to exclude breaches traced to unsupported software. Premiums spike or coverage gets refused.

Business continuity

You become the easy target.

Once Microsoft stops patching, every disclosed CVE is a public roadmap. Threat actors deliberately prioritise EOL systems because the time-to-exploit is days, not months.

Pick the path that fits

Three packages. One that's right for you.

Every Melbourne SMB we've migrated falls into one of these three. Read the "when" line, pick the closest match, see the price.

Just want the server off the wall by 2027

10–25 staff · 1 physical server · email + file share are the only critical workloads

Quick Lift Server Retirement

$6,900 · 4 weeks

See package details
⭐ Most popular

Want to move properly to the cloud

15–50 staff · ready to retire the server room · need M365 + SharePoint + modern endpoint management

Modern Workplace Migration

$14,500 · 8 weeks

See package details

Have line-of-business apps that must stay on Windows Server

30–100 staff · custom LOB workload · scaling plan in cloud

Strategic Cloud Landing Zone

$29,000 · 12 weeks

See package details

A typical 8-week migration

What we do, week by week.

Week 1

Discovery & decision

Read-only audit of your server, M365 tenant, applications. We confirm package fit and lock the SOW.

Week 2–3

M365 + identity foundation

Tenant hardened, MFA enforced, mailbox migration prepared. Conditional Access baseline applied.

Weekend

Cutover (Fri eve → Mon morning)

Mailbox + file-share cutover happens overnight. Staff log in Monday to new locations with a 30-min walk-through.

Week 4–8

Backup, DR, training, handover

Immutable Sydney backup configured + tested. DR plan documented. Staff training session. Old server formally decommissioned.

Frequently asked

The questions we get every week.

Can't I just buy Microsoft Extended Security Updates (ESU) instead?
You can — but ESU is roughly $1,000–$3,000 per server per year, only buys you up to 3 years of patches, and Microsoft prices the second and third year higher than the first. The total ESU spend on a single server typically gets you halfway to a full migration cost. ESU is the right answer only when a specific workload truly cannot be moved (e.g. a legacy LOB app without a vendor upgrade path). For everything else, the migration math wins.
How long does a 25-user migration realistically take?
Quick Lift Server Retirement: 4 weeks elapsed (most clients see staff back to normal work the Monday after cutover). Modern Workplace Migration: 8 weeks for the full project including SharePoint migration and modern device management. We do the disruptive work overnight on a weekend; staff downtime is typically zero.
Will my LEAP / Xero / MYOB / practice management software survive the move?
Yes — these are all cloud-native or cloud-tolerant. LEAP runs from the browser. Xero and MYOB Online are pure SaaS. The only software we flag is on-prem-only LOB apps from small vendors that have not modernised. We identify those in week 1 and you get a written list of what needs an alternative path before we start.
Do I have to migrate everything to Azure?
No. Most Melbourne SMBs we move end up with: Microsoft 365 for email, OneDrive, SharePoint, Teams (no Azure VM). Quick Lift keeps a single Azure VM if you have one workload that needs Windows Server. Strategic Cloud is for businesses that genuinely need an Azure landing zone for LOB apps — that's the minority.
What if we miss the 12 January 2027 deadline?
Three things happen. First, no more security updates — every published CVE is exploitable forever. Second, your cyber insurance renewal flags it; expect either a premium hike or a coverage exclusion for breaches involving the EOL system. Third, you can buy ESU as a bridge for up to 3 years, but the cost stacks year-on-year. We can still migrate you after the deadline; the project is the same. The cost of waiting is exposure.
What about Server 2019 and 2022?
Server 2019 reaches EOL January 2029. Server 2022 with Azure Hybrid Benefit + Azure ESU is the modern target if you need Windows Server at all. Server 2019 customers have time but the same migration logic applies — the conversation is just less urgent.
Can you handle the Azure billing too?
Either way. Most clients put the Azure subscription under our CSP agreement so there's a single consolidated bill and we have cost-optimisation visibility. If you prefer to keep Microsoft direct, the Azure subscription stays in your tenant and we just operate it.
What does it cost after migration?
Recurring managed IT starts at $79/user/mo (Essential plan) and scales to $169/user/mo (Secure+). Azure consumption (if you have a VM or landing zone) is passed through at cost — typically $200–$2,500/mo depending on workload. Microsoft 365 licensing is at Microsoft list price, no margin from us. We publish all 29 prices on our pricing page.
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